Synthesis of annulated 2H-indazoles and 1,2,3- and 1,2,4-triazoles via a one-pot palladium-catalyzed alkylation/direct arylation reaction.
A variety of six-membered-ring annulated 2H-indazoles and 1,2,3- and 1,2,4-triazoles were synthesized in good to excellent yields from the corresponding bromoethyl azoles and aryl iodides. The annulation process involves a one-pot norbornene-mediated palladium-catalyzed sequence whereby an alkyl-aryl bond and an aryl-heteroaryl bond are successively formed through two C-H bond activations. Subsequent functionalizations of the resulting polycyclic through cross-coupling reactions are also presented.
Laleu
Benoît
B
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario, M5S 3H6, Canada.
Lautens
Mark
M
D000478:Alkylation; D002384:Catalysis; D007191:Indazoles / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D007191:Indazoles; D014230:Triazoles; D010165:Palladium